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Cell Death / Apoptosis / Autophagy
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ALX-306-019 Revised 06-Feb-05
Nervonic ceramide
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SYNONYMS 15-Tetracosenamide
PRODUCT LINE Neurobiology
PRODUCT CATEGORY Ceramides / Cerebrosides / Sphingolipids / Related Products
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ALX-306-019-M005   5 mg 85.00 USD Add To Cart
Product Specification
FORMULA: C42H82NO3
MW: 648.1
CAS NUMBER: 54164-50-0
SOURCE/HOST: Synthetic.
PURITY: ≥98%
APPEARANCE: White crystalline solid.
SOLUBILITY: Soluble in DMSO, dimethyl formamide or 100% ethanol.
SHIPPING: SHIPPED ON BLUE ICE
LONG TERM STORAGE: -20°C

Product Description
Naturally occurring ceramide and an integral part of the sphingomyelin cycle [1]. C24-N-acyl sphingosines are the most abundant ceramide species in human plasma [2] and in rabbit leukocytes [3], where they make up to 50-60% of total ceramides. Nervonic ceramide stimulates the proliferation of basophilic erythroblasts, suggesting a possible role in erythrocyte maturation [3].
Product Specific Literature References
[1] Ceramide signalling and the immune response: L.R. Ballou, et al.; Biochim. Biophys. Acta 1301, 273 (1996), (Review) Abstract
[2] Identification and quantitative determination of ceramides in human plasma: K. Samuelsson; Scand. J. Clin. Lab. Invest. 27, 371 (1971) Abstract
[3] Stimulation of erythroblast maturation in vitro by sphingolipids: R.B. Clayton, et al.; J. Lipid Res. 15, 557 (1974) Abstract
 
 
ALX-306-020 Revised 22-Sep-08
Lignoceric ceramide
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SYNONYMS Tetracosenamide
PRODUCT LINE Neurobiology
PRODUCT CATEGORY Ceramides / Cerebrosides / Sphingolipids / Related Products
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ALX-306-020-M005   5 mg 85.00 USD Add To Cart
Product Specification
FORMULA: C42H83NO3
MW: 650.1
CAS NUMBER: 34435-05-7
SOURCE/HOST: Synthetic.
PURITY: ≥98%
APPEARANCE: White to off-white crystalline solid.
SOLUBILITY: 20mg/ml soluble in 100% ethanol, DMSO or dimethyl formamide; also soluble in aqueous buffers.
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C
USE/STABILITY: Stable for at least 1 year after receipt when stored at -20°C. We do not recommend storing aqueous solutions for more than one day.

Product Description
Naturally occurring ceramide and an integral part of the sphingomyelin cycle [1]. C24-N-acyl sphingosines are the most abundant ceramide species in human plasma [2] and in rabbit leukocytes [3], where they make up to 50-60% of total ceramides. Lignoceric ceramide stimulates the proliferation of basophilic erythroblasts, suggesting a possible role in erythrocyte maturation [3].
Product Specific Literature References
[1] Ceramide signalling and the immune response: L.R. Ballou, et al.; Biochim. Biophys. Acta 1301, 273 (1996), (Review) Abstract
[2] Identification and quantitative determination of ceramides in human plasma: K. Samuelsson; Scand. J. Clin. Lab. Invest. 27, 371 (1971) Abstract
[3] Stimulation of erythroblast maturation in vitro by sphingolipids: R.B. Clayton, et al.; J. Lipid Res. 15, 557 (1974) Abstract
 
 
ALX-306-022 Revised 07-Feb-05
D-erythro-Sphingosine chloride, N,N,N-Trimethyl-
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SYNONYMS N,N,N-Trimethyl-D-erythro-sphingosine chloride
PRODUCT LINE Neurobiology
PRODUCT CATEGORY Ceramides / Cerebrosides / Sphingolipids / Related Products
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ALX-306-022-M005   5 mg 90.00 USD Add To Cart
Product Specification
FORMULA: C21H44ClNO2
MW: 378.0
SOURCE/HOST: Synthetic.
APPEARANCE: White crystalline solid.
SOLUBILITY: Soluble in water, methanol or DMSO; slightly soluble in chloroform.
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C
HANDLING: Keep under inert gas. Hygroscopic.

Product Description
Stable N-methylated derivative of sphingosine that exhibits antitumor and anti-inflammatory properties and inhibits platelet activating factor (PAF) activation and protein kinase C (PKC) activity. Inhibits IL-1β-induced NF-κB activation and cell surface expression of crucial selectins which promote adhesion of Lex- or sialosyl-Lex-expressing cells with platelets and endothelial cells.
Product Specific Literature References
Downregulation of GMP-140 (CD62 or PADGEM) expression on platelets by N,N-dimethyl and N,N,N-trimethyl derivatives of sphingosine: K. Handa, et al.; Biochemistry 30, 11682 (1991) Abstract
Cell membrane signaling as target in cancer therapy. II: Inhibitory effect of N,N,N-trimethylsphingosine on metastatic potential of murine B16 melanoma cell line: H. Okoshi, et al.; Cancer Res. 51, 6019 (1991) Abstract
Effect of sphingosine and its N-methyl derivatives on oxidative burst, phagokinetic activity, and trans-endothelial migration of human neutrophils: S. Kimura, et al.; Biochem. Pharmacol. 44, 1585 (1992) Abstract
Liposomal N,N,N-trimethylsphingosine (TMS) as an inhibitor of B16 melanoma cell growth and metastasis with reduced toxicity and enhanced drug efficacy compared to free TMS: cell membrane signaling as a target in cancer therapy III: Y.S. Park, et al.; Cancer Res. 54, 2213 (1994) Abstract
N,N,N-trimethylsphingosine inhibits interleukin-1 beta-induced NF-kappa B activation and consequent E-selectin expression in human umbilical vein endothelial cells: A. Masamune, et al.; FEBS Lett. 367, 205 (1995) Abstract
Lysophosphatidylcholine promotes P-selectin expression in platelets and endothelial cells. Possible involvement of protein kinase C activation and its inhibition by nitric oxide donors: T. Murohara, et al.; Circ. Res. 78, 780 (1996) Abstract; Full Text
 
 
ALX-306-023 Revised 05-Feb-08
D-erythro-Sphingosine, N-Stearoyl- (synthetic)
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SYNONYMS N-Stearoyl ceramide (synthetic)
C18-Ceramide (synthetic)
PRODUCT LINE Neurobiology
PRODUCT CATEGORY Ceramides / Cerebrosides / Sphingolipids / Related Products
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ALX-306-023-M001   1 mg 25.00 USD Add To Cart
ALX-306-023-M005   5 mg 75.00 USD Add To Cart
Product Specification
FORMULA: C36H71NO3
MW: 565.9
CAS NUMBER: 2304-81-6
SOURCE/HOST: Synthetic.
PURITY: ≥97%
APPEARANCE: White to off-white powder.
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C

 
 
ALX-306-024 Revised 13-Dec-04
D-erythro-Sphingosine, N-Acetyl-
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SYNONYMS N-Acetyl-D-erythro-sphingosine
C2-Ceramide
PRODUCT LINE Neurobiology
PRODUCT CATEGORY Ceramides / Cerebrosides / Sphingolipids / Related Products
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ALX-306-024-M005   5 mg 65.00 USD Add To Cart
ALX-306-024-M025   25 mg 260.00 USD Add To Cart
Product Specification
FORMULA: C20H39NO3
MW: 341.5
CAS NUMBER: 3102-57-6
SOURCE/HOST: Synthetic.
PURITY: ≥98%
APPEARANCE: White powder.
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C
Product Description
Induces cell differentiation.
Product Specific Literature References
Ceramide-mediated biology. Determination of structural and stereospecific requirements through the use of N-acyl- phenylaminoalcohol analogs: A. Bielawska, et al.; J. Biol. Chem. 267, 18493 (1992) Abstract; Full Text
 
 
ALX-306-025 Revised 08-Jan-08
D-erythro-Sphingosine, N-Palmitoyl- (synthetic)
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SYNONYMS N-Hexadecanoyl-D-erythro-sphingosine (synthetic)
N-Palmitoyl ceramide (synthetic)
C16-Ceramide (synthetic)
PRODUCT LINE Neurobiology
PRODUCT CATEGORY Ceramides / Cerebrosides / Sphingolipids / Related Products
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ALX-306-025-M001   1 mg 25.00 USD Add To Cart
ALX-306-025-M005   5 mg 75.00 USD Add To Cart
Product Specification
FORMULA: C34H67NO3
MW: 537.9
CAS NUMBER: 24696-26-2
SOURCE/HOST: Synthetic.
PURITY: ≥98%
APPEARANCE: White to off-white powder.
SOLUBILITY: Soluble in 100% ethanol.
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C

 
 
ALX-306-026 Revised 23-Sep-05
Neutral Glycosphingolipids (human granulocytes)
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PRODUCT LINE Neurobiology
PRODUCT CATEGORY Ceramides / Cerebrosides / Sphingolipids / Related Products
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ALX-306-026-M001   1 mg 75.00 USD Add To Cart
Product Specification
PURITY: ≥95% (TLC)
APPEARANCE: White substance.
SOLUBILITY: Soluble (1mg/ml) in chloroform/methanol (2/1, v/v).
SHIPPING: SHIPPED ON BLUE ICE
LONG TERM STORAGE: -20°C
HANDLING: Keep under inert gas.
Product Description
Mixture of neutral glycosphingolipids containing the following major compounds:
  - Lactosylceramide (d18:1, C16:0)                      MW: 861.6
  - Lactosylceramide (d18:1, C24:1)                      MW: 971.7
  - neoLactotetraosylceramide (d18:1, C16:9)      MW: 1226.8
  - neoLactotetraosylceramide (d18:1, C24:1)      MW: 1336.9

LacCer and nLc4Cer play an important role in carbohydrate-carbohydrate mediated cell adhesion, Lewisx-Lewisx-interactions, mediate cell aggregation. LacCer is also a common receptor of pathogenic bacteria.
Product Specific Literature References
Selective detection of terminally alpha 2-3 and alpha 2-6 sialylated neolacto-series gangliosides by immunostaining on thin layer chromatograms: J. Müthing & U. Neumann; Biomed. Chromatogr. 7, 158 (1993) Abstract
Nondestructive detection of neutral glycosphingolipids with lipophilic anionic fluorochromes and their employment for preparative high-performance thin-layer chromatography: J. Müthing & S.E. Kemminer; Anal. Biochem. 238, 195 (1996) Abstract
Isolation and structural characterization of glycosphingolipids of in vitro propagated bovine aortic endothelial cells: S. Duvar, et al.; Glycobiology 7, 1099 (1997) Abstract
Cell adhesion, spreading, and motility of GM3-expressing cells based on glycolipid-glycolipid interaction: N. Kojima & S.I. Hakomori; J. Biol. Chem. 266, 17552 (1991) Abstract; Full Text
N. Kojima, et al.; J. Biol. Chem. 267, 17264 (1992) Abstract; Full Text
Globoside-dependent adhesion of human embryonal carcinoma cells, based on carbohydrate-carbohydrate interaction, initiates signal transduction and induces enhanced activity of transcription factors AP1 and CREB: Y. Song, et al.; J. Biol. Chem. 273, 2517 (1998) Abstract; Full Text
Specific interaction between Lex and Lex determinants. A possible basis for cell recognition in preimplantation embryos and in embryonal carcinoma cells: I. Eggens, et al.; J. Biol. Chem. 264, 9476 (1989) Abstract; Full Text
Lex glycosphingolipids-mediated cell aggregation: M. Boubelik, et al.; Glycobiology 8, 139 (1998) Abstract
J. Angström, et al.; Glycobiology 8, 297 (1998) Abstract
General Information
BACKGROUND/TECHNICAL INFORMATION Note: Double bands on TLC-plates due to substitution of the sphingosine moiety with C16:0- and C24:1- fatty acids (lower and upper band, respectively). Lewisx-positive neutral GSL with nLc6Cer-, nLc8Cer- and nLc10Cer-cores (approx. 5 %) were detected with CD15 antibodies by TLC immunostaining.
 
 
ALX-306-028 Revised 05-May-08
Isoglobotrihexosylceramide
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SYNONYMS iGb3
PRODUCT LINE Immunology
PRODUCT CATEGORY Natural Killer T [NKT] Cells / Related Products
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ALX-306-028-C100   100 µg 85.00 USD Add To Cart
ALX-306-028-M001   1 mg 455.00 USD Add To Cart
Product Specification
FORMULA: C62H117NO18
MW: 1164.6
PURITY: ≥95% (1H-NMR)
APPEARANCE: White to off-white powder.
SOLUBILITY: Soluble in pyridine or chloroform:methanol (2:1).
SHIPPING: SHIPPED ON BLUE ICE
SHORT TERM STORAGE: +4°C
LONG TERM STORAGE: -20°C

Product Description
Lysosomal glycosphingolipid proposed to be the natural ligand of NKT cells. Stimulates natural killer T (NKT) cells similar to α-GalCer. For negative control compound see globotrihexosylceramide (Gb3) (Prod. No. ALX-306-030).
Product Specific Literature References
[1] Lysosomal glycosphingolipid recognition by NKT cells: D. Zhou, et al.; Science 306, 1786 (2004) Abstract
[2] Synthesis and biological evaluation of alpha-galactosylceramide (KRN7000) and isoglobotrihexosylceramide (iGb3): C. Xia, et al.; Bioorg. Med. Chem. Lett. 16, 2195 (2006) Abstract
[3] Chemoenzymatic Syntheses of iGb3 and Gb3: Q. Yao et al.; Org. Lett. 8, 911 (2006) Abstract
General Information
BACKGROUND/TECHNICAL INFORMATION Solubilization:
Our recommendation is to dissolve product in chloroform: abs. methanol 2:1. Aliquot into glass tubes, dry and store at 4°C. Resuspended in abs. methanol (at concentrations not higher than 1%) prior to cell assays. Note: The use of DMSO may abolish the iGb3 activity and should be avoided [2].

For expanding human NKT cells from freshly isolated peripheral blood mononuclear cells (PBMC):
Mix iGb3 at 100ng/ml with PBMC and culture for 4-5 days.

For the stimulation of mouse NKT cells:
The bone marrow derived dendritic cells (BMDC) is the most efficient cell type that present iGb3. Use 50’000-250’000 of BMDCs pulsed overnight with 100ng/ml of iGb3 and 50’000 freshly purified NKT cells as a responder. Use tetramer sorting to purifiy the NKT cells from spleen and before mixing with BMDCs, rest them in culture medium for 12 hours and then wash with medium to avoid a high background. MACS sorting technique is not recommended. Alternatively, NKT cell hybridomas can be used to detect the ligand. (For reference see: http://home.uchicago.edu/~dzhou/Testing%20iGb3%20ligand.htm)
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Further Categories Containing This Product:
Ceramides / Cerebrosides / Sphingolipids / Related Products
 
 
ALX-306-029 Revised 21-Oct-08
OCH
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SYNONYMS (2S,3S,4R)-1-O-(α-D-Galactopyranosyl)-2-tetracosanoyl-
aminononan-3,4-diol
PRODUCT LINE Immunology
PRODUCT CATEGORY Natural Killer T [NKT] Cells / Related Products
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ALX-306-029-C250   250 µg 120.00 USD Add To Cart
ALX-306-029-M001   1 mg 250.00 USD Add To Cart
Product Specification
FORMULA: C39H78NO9
MW: 704.1
PURITY: ≥95% (1H-NMR)
APPEARANCE: White to off-white powder.
SOLUBILITY: Soluble in DMSO, 100% ethanol (warm) or methanol (warm).
SHIPPING: SHIPPED ON BLUE ICE
SHORT TERM STORAGE: +4°C
LONG TERM STORAGE: -20°C
HANDLING: After reconstitution, aliquot into glass vials.

Product Description
Truncated analog of α-Gal-Cer. Selectively induces IL-4, as opposed to IFN-γ. Offers protection in mouse against experimental autoimmune encephalomyelitis (EAE), an animal model of multiple sclerosis. Also offers protection against diabetes in NOD mice and against collagen induced arthritis. Stimulation of NKT cells with α-Gal-Cer results in release of a mixture of Th1 and Th2 cytokines, stimulation with OCH results in release of primarily Th2 cytokine.
Product Specific Literature References
Synthesis and evaluation of sphinganine analogues of KRN7000 and OCH: R.M. Ndonye, et al.; J. Org. Chem. 70, 10260 (2005) Abstract
Total synthesis of an immunosuppressive glycolipid, (2S,3S,4R)-1-O- (alpha-d-galactosyl)-2- tetracosanoylamino-1,3,4-nonanetriol: K. Murata, et al.; J. Org. Chem. 70, 2398 (2005) Abstract
Glycolipids for natural killer T cells: P.B. Savage, et al.; Chem. Soc. Rev. 351, 771 (2006) Abstract
Further Categories Containing This Product:
Ceramides / Cerebrosides / Sphingolipids / Related Products
 
 
ALX-306-030 Revised 06-Dec-06
Globotrihexosylceramide
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SYNONYMS Gb3
PRODUCT LINE Immunology
PRODUCT CATEGORY Natural Killer T [NKT] Cells / Related Products
Ordering Information
Product Numbers: Format: Size: Unit Price: Quantity: Add To Cart
ALX-306-030-C100   100 µg 85.00 USD Add To Cart
ALX-306-030-M001   1 mg 455.00 USD Add To Cart
Product Specification
FORMULA: C62H117NO18
MW: 1164.6
PURITY: ≥95% (1H-NMR)
APPEARANCE: White to off-white powder.
SOLUBILITY: Soluble in pyridine or chloroform:methanol (2:1).
SHIPPING: SHIPPED ON BLUE ICE
SHORT TERM STORAGE: +4°C
LONG TERM STORAGE: -20°C

Product Description
Negative control for isoglobotrihexosylceramide (iGb3) (Prod. No. ALX-306-028). Does not stimulate natural killer T (NKT) cells.
Product Specific Literature References
Chemoenzymatic Syntheses of iGb3 and Gb3: Q. Yao et al.; Org. Lett. 8, 911 (2006) Abstract
General Information
BACKGROUND/TECHNICAL INFORMATION Solubilization:
Our recommendation is to dissolve product in chloroform: abs. methanol 2:1. Aliquot into glass tubes, dry and store at 4°C. Resuspended in abs. methanol (at concentrations not higher than 1%) prior to cell assays.
Further Categories Containing This Product:
Ceramides / Cerebrosides / Sphingolipids / Related Products